A medium-chain fatty acid comprising hexanoic acid carrying a 5-oxo group.

Identification

IUPAC Names

5-oxohexanoic acid

Molecular Formula
C6H10O3
Mass
130.14180
Monoisotopic Mass
130.06299
Charge
0
InChI
InChI=1S/C6H10O3/c1-5(7)3-2-4-6(8)9/h2-4H2,1H3,(H,8,9)
InChIKey
MGTZCLMLSSAXLD-UHFFFAOYSA-N
SMILES
CC(=O)CCCC(O)=O
Synonyms

4-acetyl-butanoic acid

4-acetyl-butyric acid

4-Acetylbutyric acid

5-keto-n-caproic acid

5-Ketocaproic acid

5-Ketohexanoic acid

5-oxocaproic acid

5-Oxohexanoate

5-Oxohexanoic acid

delta-Ketocaproic acid

delta-Oxocaproic acid

gamma-Acetylbutyric acid

Species

homo sapiens

NCBI:txid9606Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.

Europe PubMed Central results


Enzyme reactions involved in anaerobic cyclohexanol metabolism by a denitrifying Pseudomonas species.

Author: Dangel W, Tschech A, Fuchs G.

Abstract: The enzymes involved in the anaerobic degradation of cyclohexanol were searched for in a denitrifying Pseudomonas species which metabolizes this alicyclic compound to CO2 anaerobically. All postulated enzyme activities were demonstrated in vitro with sufficient specific activities. Cyclohexanol dehydrogenase catalyzes the oxidation of the substrate to cyclohexanone. Cyclohexanone dehydrogenase oxidizes cyclohexanone to 2-cyclohexenone. 2-Cyclohexenone hydratase and 3-hydroxycyclohexanone dehydrogenase convert 2-cyclohexenone via 3-hydroxycyclohexanone into 1,3-cyclohexanedione. Finally, the dione is cleaved by 1,3-cyclohexanedione hydrolase into 5-oxocaproic acid. Some kinetic and regulatory properties of these enzymes were studied.

The metabolism of n-octane in Fischer 344 rats.

Author: Olson CT, Yu KO, Hobson DW, Serve MP.

Abstract: The urinary metabolites of n-octane in Fischer 344 rats given the hydrocarbon by gavage included 2-octanol, 3-octanol, 5-oxohexanoic acid, and 6-oxoheptanoic acid. The sex of the animals influenced the relative amounts of metabolites formed. Analyses were performed by gas-liquid chromatography (GC) and gas-liquid chromatography/mass spectrometry (GC/MS). This is the first reported finding of keto acids in hydrocarbon oxidative metabolism. No kidney damage was found as a result of n-octane dosing although the 2,2,4-trimethylpentane (iso-octane) isomer does cause kidney lesions in male rats.